Annie and I always had a special relationship. She gave me the scoop on all the girls that worked under me and let me know what was going on in the mind of each of them. What was their relationship status? What was their income situation? In essence, she fed me all of the important details I needed to find my way into their panties.

Annie was closer to my age, 42 in fact and well preserved for her age. She was married with a couple of kids (already out of the house) and stuck in a somewhat less than fulfilling relationship at home. Her husband didn’t make a lot of money and didn’t seem to want to either. Annie had been with the company for quite a while, much longer than I, and was doing pretty well for herself if you took into account her salary, benefits, and a sizable balance in her 401(k) account. She really didn’t need her husband’s meager income to get by and this gave her a sense of independence and freedom to be herself whenever she wanted to.

Annie often accompanied our department on our weekly happy hour excursions. The more I was around her the more I became attracted to her. She had long curly blond hair, actually sort of dishwater blond, wore a lot of sundresses and generally had that wholesome 60’s-like hippy aura about her. She ate a lot of wholesome foods and generally was a health nut, but her one downfall was that she enjoyed a glass of red wine whenever she could. I always made sure she didn’t pay for a drink when she went with us and I always made sure her glass was full.

My waitress friend Tammie, our regular server at our local watering hole and occasional lesbian lover of one of my girls, Susan, noticed I was making sure the wine kept a steady flow and I could tell she sensed that I was on the prowl. “Got a new target tonight, John?” she whispered in my ear as she refilled Annie’s glass for the third time. I had made sure that Annie joined us at this particular happy hour as I had sensed earlier in the day that I might have an opening. I had dropped by Annie’s office around 9:30 to get a little scoop on a new girl I had spotted on another floor earlier that day. She took me back to the file room where all of the employee records were kept and pulled on the drawer containing the new girl’s file.

“Here you go fuck head,” she blasted. “Don’t you ever get tired of fucking the help?” I could sense a bit of frustration in her tone as usually she just grinned at me with a seductive smile and then left me alone with the file so I could get the data I needed. “Don’t you ever consider that there are plenty of people closer to your own age with needs to be filled? Why are you always looking to fuck the young new hires? Damn John, you’re such an inconsiderate bastard. Why don’t you just go in the men’s room and jack off?”

Holy shit. What had I done, or not done, to piss this woman off? Annie turned quickly and started to walk out of the file room as I tried to assess her comments. A man’s mind doesn’t always work as fast as it should but my instincts did usually react quickly enough. I reached for her arm as she started to walk away, her flimsy little dress swirling around her lovely legs as she tried to make her getaway. “Whoa, girl. What the fuck was that all about? Something going on that I need to know about?”

“God John. Are you a totally dense fuck? Every week you come in here wanting information on some pretty young chic that you usually end up banging. I could only wish my sex life was that exciting. Do you know how much trouble I would be in if one of those girls found out that I had supplied you with intimate details about them for you to use to your advantage? I can’t afford to lose this job with the mess I have at home. And it isn’t exactly a thrill knowing you’re getting fucked all the time while I risk my job for you and end up with nothing but a dildo in my cunt at night. Why don’t you find me someone to play with and return the favor? You’re just a typical dickhead male. All of you are a bunch of fucking bastards!”

Annie lowered her face into her hands and started to sob slowly. My slow male brain now registered the issue. Things weren’t good at home. I knew that already but they must have taken an even sharper turn for the worse. Annie was a beautiful woman. I guess in current terms you would label her a “cougar”. At 42 her body was in fantastic shape. She had nice perky tits, very shapely legs, a tight ass, and she almost always had a smile on her face. There was nothing not to like about Annie, nothing at all. In fact, I had more than once ended up in the bathroom jacking off to the smell of her light perfume after one of our file room sessions.

“Hey, Annie, what’s wrong?” I asked as she tried to compose herself.

“Fuck you, John. Just fuck you!” She obviously wasn’t herself and I felt the need to pursue the discussion.

I took her in my arms and felt her head lay against my shoulder. I held her for a moment without saying anything more. I wasn’t sure I had the right words so I decided not to risk another comment. I felt her slim body and her nice tits against me as I held her. There really wasn’t much between that sundress and my cock. This was the first time we had shared anything remotely resembling an embrace and it felt good, even if the situation was not optimal. I pulled my face back so I could see hers and looked into her teary eyes. “Hey, I know I’m nothing but a dickhead but how would you like to join our group tonight for happy hour?”

She smiled and wiped a tiny tear from under her eye. “That would be nice”, she replied in a soft voice. “I’m sorry I went off on you John. Maybe we can talk about it tonight.” Then she did something that cluttered my mind the rest of the day. As we pulled apart from each other she gave me a kiss on the lips, not a peck mind you, but a very deliberate and passionate kiss on the lips. I left without obtaining the file that I had come for but I sensed that I might be leaving with something equally as valuable.

Back at the bar I was enjoying the wine at an equal pace with Annie. Some of the other ladies had joined us that night – Susan and Debbie, and my most recent conquest, Cindy. All of these ladies had proven to be voracious sexual partners and one would think that there would be a bit of cat fighting or jealousy among the group, but no such condition existed. In fact, the girls chatted amicably during the night, occasionally winking at me from time to time or giggling to each other about something. My mind could only dream about what stories they might have shared about their sessions with me. The only rationale I could come up with for this congenial atmosphere was my age and marital status – 55 and hitched. I guess none of them saw me as anything more than a detached roll in the hay. Ok by me, or at least it was tonight.

I sat next to Annie and made sure our bodies were in contact with one another. I wanted to put my hand on her thigh under the table but I hadn’t had enough wine and my courage was lacking. “So tell me what was on your mind today when I came by your office. That was an awkward scene in the file room.” I thought my comments were gentle enough to get her talking about her feelings but not too overly pushy to make her withdraw. She was ahead of me by maybe a drink or two and her courage was at a much higher level than mine.

“I want you to fuck me John, …tonight.” Wow. Her direct request registered immediately in my crotch but not so clearly in my mind. Her hand rested on my inner thigh, slightly contacting the head of my instant erection. “You’ve fucked everyone at this table except me. I don’t think that’s quite right.